W.r.t your query, I have gone through it and tried to replicate it.
Few observations which I found are that :-

1) Yes, working with Odoo POS is possible in off-line mode only if
your Internet connection gets lost during any session. In this case
the browser cache stores the information until the internet
connection restores.

2) But for the very first time Internet connection is always required
to connect with the server in order to start with/load the data. In
your case, if you restart your PC it means system is restarting hence
Internet connection would be required as the data would load again
from the beginning.

3)This is because Odoo has the capability to work off-line even if
your Internet connection gets lost only if you are in the mid of any
session and you need to continue with other orders as your customers
might be waiting in queue for their orders to be processed. In this
case the browser cache stores the information until the Internet
connection restores.

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